Publication detail

Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer

Authors: Panov Illia | Drabina Pavel | Hanusek Jiří | Sedlák Miloš

Year: 2013

Type of publication: článek v odborném periodiku

Name of source: Synlett

Publisher name: Georg Thieme Verlag KG

Place: Stuttgart

Page from-to: 1280-1282

Titles:

Language	Name	Abstract	Keywords
cze	Stereoselektivní syntéza klíčového intermediátu inhibitoru HIV Proteasy Fosamprenaviru a jeho diastereomeru	Vysoce stereoselektivní Henryho reakce byla použita pro syntézu prekursoru fosamprenaviru (2S,3R)-N-terc-butyl-oxycarbonyl-2-amino-3-hydroxy-1-fenyl-4-nitrobutanu a jeho 2S, 3S diasteromeru z N-tert-butyloxycarbonyl-(S)-fenylalaninalu a nitromethanu. Komplex (2S,5R)- nebo (2R,5S)-5-isopropyl-5-methyl-2-(pyridin-2-yl)imidazolidin-4-onu s octanem měďnatým byl použit jako katalyzátor a poskytl produkt s absolutní konfigurací 2S,3R (dr = 90: 10, celkový výtěžek 89%) resp. 2S,3S (dr = 99: 1, celkový výtěžek 94%).	Stereoselektivní syntéza; Fosamprenaviru
eng	Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer	Highly stereoselective Henry reaction has been used in the synthesis of the fosamprenavir precursor (2S,3R)-N-tert-butyl-oxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane and its 2S, 3S diasteromer from N-tert-butyloxycarbonyl-(S)-phenylalaninal and nitromethane. The complex of (2S,5R)- or (2R,5S)-5-isopropyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one with copper(II) acetate has been used as the catalyst which provided the product with 2S,3R absolute configuration (dr = 90: 10, overall yield 89%) or 2S,3S (dr = 99: 1, overall yield 94%), respectively.	aldol reaction; diastereoselectivity; HIV; homogenous catalysis; ligands

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